Iodine → HCID 86639252, compound

A solution of 1-chloro-4-methoxy-butane (8.19 g, 66.8 mmol) in abs. ether (12 ml) was added, under an argon atmosphere and with intermittent heating, to magnesium (1.62 g, 66.8 mmol) and I2 in abs. diethyl ether (25 ml). The mixture was stirred for 1 h under reflux until the magnesium had largely dissolved. While cooling with ice, a solution of 8-dimethylamino-1,4-dioxa-spiro[4.5]decane-8-carbonitrile B-1 (10.5 g, 50.1 mmol) in abs. THF (40 ml) was added dropwise. A viscous precipitate formed, and further abs. THF (20 ml) was added for the purpose of better mixing. The mixture was stirred for 24 h at room temperature. NH4Cl solution (20%, 80 ml) and water (100 ml) were added to the mixture, while cooling with ice, the organic phase was separated and the aqueous phase was extracted with ether (3×100 ml). The combined organic phases were washed with saturated NaCl solution (80 ml) and water (80 ml), dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography with chloroform/methanol (50:120:19:1).

1. dissolutionhad largely dissolved
2. temperatureWhile cooling with ice
3. customA viscous precipitate formed
4. additionof better mixing
5. stirringThe mixture was stirred for 24 h at room temperature
6. temperaturewhile cooling with ice
7. customthe organic phase was separated
8. extractionthe aqueous phase was extracted with ether (3×100 ml)
9. washThe combined organic phases were washed with saturated NaCl solution (80 ml) and water (80 ml)
10. dry with materialdried over Na2SO4
11. concentrationconcentrated in vacuo
12. customThe crude product was purified by flash chromatography with chloroform/methanol (50:120:19:1)

ORD record

ord-f2a1bb6cf91143cea0add97ae5bcdd2b

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08404740B2